Heterocyclic substituted 4-benzoyl-pyrazole as herbicides

ABSTRACT

Substituted 4-benzoylpyrazole of the formula I                    
     where: 
     Q is a pyrazole of the formula II                    
     X 1  is a straight-chain or branched C 1 -C 6 -alkylene, a C 2 -C 6 -alkenylene or a C 2 -C 6 -alkynylene chain which is interrupted by a hetero atom selected from the group consisting of: 
     oxygen and sulfur, 
     Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups: 
     nitrogen, 
     oxygen in combination with at least one nitrogen or 
     sulfur in combination with at least one nitrogen; 
     and agriculturally useful salts thereof, processes and intermediates for preparing compounds of the formula I, compositions comprising them and the use of the compounds of the formula I and of compositions comprising them for controlling harmful plants are described.

This application is a 371 of PCT/EP98/04635 Jul. 23, 1998 now WO 99/10328 Mar. 4, 1999.

The present invention relates to substituted 4-benzoylpyrazoles of the formula I

where:

R¹ and R² are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, —OR³, —OCOR³, —OSO₂R³, —S(O)_(n)R³, —SO₂OR³, —SO₂N(R³)₂, —NR³SO₂R³ or —NR³COR³;

R³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl; where the abovementioned alkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R³, —OR³, —SR³, —N(R³)₂, ═NOR³, —OCOR³, —SCOR³, —NR³COR³, —CO₂R³, —COSR³, —CON(R³)₂, C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted;

n is 0, 1 or 2;

Q is a pyrazole of the formula II

 which is attached in position 4 and where

R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl;

R⁵ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, phenyl or phenyl which may be partially or fully halogenated and/or may carry one to three of the following radicals:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

R⁶ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl, phenoxycarbonyl or phenylsulfonyl,

where the four last-mentioned substituents are unsubstituted, or the phenyl ring in question may be partially or fully halogenated and/or may carry one to three of the following radicals:

nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

X¹ is a straight-chain or branched C₁-C₆-alkylene, a C₂-C₆-alkenylene or a C₂-C₆-alkynylene chain which is interrupted by a hetero atom selected from the group consisting of:

oxygen and sulfur,

where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR⁷, —OCOR⁷, —OCONHR⁷ or —OSO₂R⁷;

R⁷ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, phenyl-C₁-C₆-alkyl, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may be substituted by one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R⁸;

R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals:

cyano, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

and agriculturally useful salts thereof.

In addition, the invention relates to processes and intermediates for preparing compounds of the formula I, to compositions comprising them, and to the use of the compounds of the formula I and of compositions comprising them for controlling harmful plants.

4-Benzoylpyrazoles are disclosed in the literature, for example in EP-A 282 944.

However, the herbicidal properties of the prior art compounds and their crop plant safety are not entirely satisfactory.

It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.

We have found this object is achieved by the 4-benzoylpyrazoles of the formula I according to the invention and their herbicidal activity.

Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.

The present invention also provides stereoisomers of the compounds of the formula I. Pure stereoisomers and also mixtures thereof are included.

Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers and, if this is the case, are present as enantiomers or mixtures of diastereomers. The invention provides the pure enantiomers or diastereomers and also mixtures thereof.

The compounds of the formula I may also be present in the form of their agriculturally useful salts, the kind of salt generally not being important. The salts of those cations or the acid addition salts of those acids whose cations or anions, respectively, do not adversely affect the herbicidal activity of the compounds I are generally suitable.

Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where, if desired, one to four hydrogen atoms may be replaced by C₁-C₄-alkyl or hydroxyl-C₁-C₄-alkyl and/or one phenyl or benzyl, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useable acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

Process A:

Reactions of pyrazoles of the formula II (where R⁶=H) with an activated carboxylic acid IIIa or a carboxylic acid IIIb, which is preferably activated in situ, to give the acylation product V, and subsequent rearrangements to the compounds of the formula Ia according to the invention.

L¹ is a nucleophilically replaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, or carboxylate, for example acetate, trifluoroacetate, etc.

The activated carboxylic acid can be employed directly, as in the case of the acyl halides, or be generated in situ, for example by using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic esters, 2-pyridine disulfite/triphenylphosphine, carbonyldiimidazole, etc.

It may be advantageous to carry out the acylation reaction in the presence of a base. The starting materials and the auxiliary base are advantageously employed in equimolar amounts. A slight excess of auxiliary base, for example 1.2 to 1.5 molar equivalents, based on II, may be advantageous under certain circumstances.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Examples of solvents which can be used are chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters such as ethyl acetate or mixtures of these.

If acyl halides are employed as activated carboxylic acid component, it may be advantageous to cool the reaction mixture to 0-10° C. when adding this reaction partner. The mixture is subsequently stirred at 20-100° C., preferably at 25-50° C., until the reaction is complete. Work-up is carried out in the customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are particularly suitable for this purpose are methylene chloride, diethyl ether and ethyl acetate. After the organic phase has been dried and the solvent has been removed, the crude enol ester of the formula V is purified, preferably by chromatography. Alternatively, it is possible to employ the crude enol ester of the formula V without further purification for the rearrangement reaction.

The rearrangement of the enol esters of the formula V to the compounds of the formula I is advantageously carried out at from 20 to 40° C. in a solvent and in the presence of a base and, if appropriate, in the presence of a cyano compound.

Examples of solvents which can be used are acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines such as triethylamine, pyridine or alkali metal carbonates, such as sodium carbonate, potassium carbonate, which are preferably employed in equimolar amounts or up to a four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonates.

Suitable cyano compounds are inorganic cyanides such as sodium cyanide, potassium cyanide and organic cyano compounds such as acetone cyanohydrin, trimethylsilyl cyanide. They are employed in an amount of 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example, in an amount of 5 to 15, preferably 10, mol percent, based on the ester.

Particular preference is given to employing alkali metal carbonates, such as potassium carbonate, in acetonitrile or dioxane.

Work-up can be carried out in a manner known per se. For example, the reaction mixture is acidified with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride, ethyl acetate. The organic phase can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified, and the precipitate which forms is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.

(Examples of the synthesis of esters from hydroxypyrazoles and the rearrangement of the esters are mentioned for example in EP-A 282 944 or U.S. Pat No. 4, 643, 757).

The pyrazoles of the formula II (where R⁶=H) used as starting materials are known or can be prepared by methods known per se (for example EP-A 240 001, J. Prakt. Chem. 315 (1973), 383).

Process B:

Reactions of 4-benzoylpyrazoles of the formula Ia with a compound of the formula IV (where R⁶≠H):

L² is a nucleophilically replaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, sulfonate, for example mesylate, triflate, etc.

The compounds of the formula IV can be employed directly, for example in the case of the alkyl halides, acyl halides, sulfonyl halides, carboxylic anhydrides and sulfonic anhydrides, or prepared in situ, for example activated carboxylic acids (by means of carboxylic acid and dicyclohexylcarbodiimide, carbonyldiimidazole, etc.).

In general, the starting materials are employed in an equimolar ratio. However, it may also be advantageous to employ an excess of one or the other component.

Where appropriate, it may be advantageous to carry out the reaction in the presence of a base. The starting materials and the auxiliary base are advantageously employed in equimolar amounts. Under certain circumstances, it may be advantageous to employ an excess of the auxiliary base, for example 1.5 to 3 molar equivalents, based on Ia.

Suitable auxiliary bases are tertiary alkylamines such as triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate, potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine, pyridine and potassium carbonate.

Examples of suitable solvents are chlorinated hydrocarbons such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide or esters, such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range of from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in a manner known per se.

The benzoic acids of the formula III are novel,

where:

R¹ and R² are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, —OR³, —OCOR³, —OSO₂R³, —S(O)_(n)R³, —SO₂OR³, —SO₂N(R³)₂, —NR³SO₂R³ or —NR³COR³;

n is 0, 1 or 2;

R³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl; where the abovementioned alkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R³, —OR³, —SR³, —N(R³)₂, ═NOR³, —OCOR³, —SCOR³, —NR³COR³, —CO₂R³, —COSR³, —CON(R³)₂, C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted;

X¹ is a straight-chain or branched C₁-C₆-alkylene, a C₂-C₆-alkenylene or a C₂-C₆-alkynylene chain which is interrupted by a hetero atom selected from the group consisting of:

oxygen and sulfur,

where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR⁷, —OCOR⁷, —OCONHR⁷ or —OSO₂R⁷;

R⁷ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, phenyl-C₁-C₆-alkyl, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may be substituted by one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R⁸;

R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals:

cyano, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

R⁹ is hydroxyl or a hydrolyzable radical.

Examples of hydrolyzable radicals are alkoxy, phenoxy, alkylthio and phenylthio radicals which can be substituted, halides, hetaryl radicals which are bonded via nitrogen, amino and imino radicals which can be substituted, etc.

Preference is given to benzoyl halides IIIa where L¹=halogen ({circumflex over (=)} III where R⁹=halogen),

where the variables R¹, R², X¹ and Het are each as defined under formula III and

L¹ is halogen, in particular chlorine or bromine.

Preference is also given to benzoic acids of the formula IIIb ({circumflex over (=)} III where R⁹=hydroxyl),

where the variables R¹, R², X¹ and Het are each as defined under formula III.

Preference is also given to benzoic esters of the formula IIIc ({circumflex over (=)} III where R⁹=C₁-C₆-alkoxy),

where the variables R¹, R², X¹ and Het are each as defined under formula III and

M is C₁-C₆-alkoxy.

The compounds of the formula IIIa (where L¹=halogen) can be synthesized by methods similar to those known from the literature (cf. L. G. Fieser, M. Fieser “Reagents for Organic Synthesis”, Vol. I, pp. 767-769 (1967)) by reacting benzoic acids of the formula IIIb with halogenating agents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride and oxalyl bromide.

The benzoic acids of the formula IIIb can be obtained, inter alia, by hydrolyzing the benzoic esters of the formula IIIc (where M=C₁-C₆-alkoxy).

The benzoic esters of the formula IIIc according to the invention can be synthesized by various methods known from the literature (for example a: G. Dittus in Houben-Weyl, Methoden der Organischen Chemie, Volume VI/3, Oxygen Compounds I, 4th Edition, 1965, p. 493 ff., Georg Thieme Verlag; b: T. L. Gilchrist, Heterocyclenchemie, 2nd Edition, Verlag Chemie, 1995), as illustrated in the examples that follow.

Process C:

Substitution of the benzoic esters VIa with suitable nucleophiles VII gives the benzoic esters IIIc according to the invention,

where M, R¹ and R² are each as defined above, L² is a suitable nucleophilically replaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, sulfonate, for example mesylate, triflate, etc.

X² is a straight-chain or branched alkylene, an alkenylene or an alkynylene chain having at least one and a maximum of five carbon atoms, where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR⁷, —OCOR⁷, —OCONHR⁷ or —OSO₂R⁷ and

X³ is a straight-chain or branched alkylene, an alkenylene or an alkynylene chain having a maximum of five carbon atoms, where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR⁷, —OCOR⁷, —OCONHR⁷ or —OSO₂R⁷.

The starting materials are usually employed in equimolar amounts. However, it may be advantageous to employ one or the other component in excess.

If appropriate, it may be advantageous to carry out the reaction in the presence of a base. The starting materials and the auxiliary base are advantageously employed in equimolar amounts. In certain cases, an excess of the auxiliary base, for example 1.5 to 3 molar equivalents, based on VIa, may be advantageous.

Suitable auxiliary bases are tertiary alkylamines such as triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine, pyridine and potassium carbonate.

Suitable solvents are, for example, chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in a manner known per se.

Process D:

Substitution of suitably substituted heterocycles VIII with benzoic esters Vb gives the benzoic esters IIIc according to the invention,

where M, R¹ and R² are each as defined above, L² is a suitable nucleophilically replaceable leaving group such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, sulfonate, for example mesylate, triflate, etc.

X² is a straight-chain or branched alkylene, an alkenylene or an alkynylene chain having at least one and a maximum of five carbon atoms, where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR⁷, —OCOR⁷, —OCONHR⁷ or —OSO₂R⁷ and

X³ is a straight-chain or branched alkylene, an alkenylene or an alkynylene chain having a maximum of five carbon atoms, where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR⁷, —OCOR⁷, —OCONHR⁷ or —OSO₂R⁷.

The starting materials are usually employed in equimolar amounts. However, it may be advantageous to employ one or the other component in excess.

If appropriate, it may be advantageous to carry out the reaction in the presence of a base. The starting materials and the auxiliary base are advantageously employed in equimolar amounts. In certain cases, an excess of the auxiliary base, for example 1.5 to 3 molar equivalents, based on VIII, may be advantageous.

Suitable auxiliary bases are tertiary alkylamines such as triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine, pyridine and potassium carbonate.

Suitable solvents are, for example, chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in a manner known per se.

Emphasis is to be given to compounds of the formula I according to the invention where the group X¹ is a C₁-C₃-alkylene, a C₂-C₃-alkenylene or C₂-C₃-alkynylene chain which is interrupted by an oxygen atom and

Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R⁸.

Furthermore, emphasis is to be given to the compounds of the formula I according to the invention where the group Het is a five- or six-membered partially or fully saturated heterocyclic or a five- or six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen;

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or substituted by RB;

R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals:

cyano, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy.

The organic moieties mentioned for the substituents R¹-R⁹ or as radicals on phenyl, hetaryl and heterocyclyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, ie. all alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, alkyliminooxy, alkoxyamino, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, alkenyl, cycloalkenyl, alkynyl moieties can be straight-chain or branched. Unless otherwise specified, halogenated substituents preferably carry one to five identical or different halogen atoms, the meaning of halogen being in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C₁-C₄-alkyl, and the alkyl moieties of C₁-C₄-alkylcarbonyl: methyl, ethyl, n-propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;

C₁-C₆-alkyl and the alkyl moieties of C₁-C₆-alkoxy-C₁-C₆-alkyl and C₁-C₆-alkylcarbonyl: C₁-C₄-alkyl as mentioned above, and also pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;

C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, eg. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;

C₁-C₆-haloalkyl and the haloalkyl moieties of C₁-C₆-haloalkylcarbonyl: C₁-C₄-haloalkyl as mentioned above, and also 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;

C₁-C₄-alkoxy and the alkoxy moieties of C₁-C₄-alkoxyamino, C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl and C₁-C₄-alkoxycarbonyl: methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

C₁-C₆-alkoxy and the alkoxy moieties of C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₂-C₆-alkyl, C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl and C₁-C₆-alkoxycarbonyl: C₁-C₄-alkoxy as mentioned above, and also pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;

C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, eg. fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;

C₁-C₄-alkylsulfonyl (C₁-C₄-alkyl-S(═O)₂—): methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;

C₁-C₆-alkylsulfonyl: C₁-C₄-alkylsulfonyl as mentioned above, and also pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C₁-C₆-haloalkylsulfonyl: a C₁-C₆-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, ie. fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(choromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromohexylsulfonyl, 6-iodohexylsulfonyl and dodecafluorohexylsulfonyl;

C₁-C₄-alkyliminooxy: methyliminooxy, ethyliminooxy, 1-propyliminooxy, 2-propyliminooxy, 1-butyliminooxy and 2-butyliminooxy;

C₃-C₆-alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl;

C₂-C₆-alkenyl: C₃-C₆-alkenyl as mentioned above, and also ethenyl;

C₃-C₆-alkynyl: prop-1-yn-1-yl, prop-2-yn-1-yl, but-1-yn-1-yl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl, pent-1-yn-1-yl, pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl, pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, hex-1-yn-1-yl, hex-1-yn-3-yl, hex-1-yn-4-yl, hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl, hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl and 4-methylpent-2-yn-5-yl;

C₂-C₆-alkynyl: C₃-C₆-alkynyl as mentioned above, and also ethynyl:

C₃-C₆-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl;

C₄-C₆-cycloalkenyl: cyclobuten-1-yl, cyclobuten-3-yl, cyclopenten-1-yl, cyclopenten-3-yl, cyclopenten-4-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl;

heterocyclyl, and also the heterocyclyl radicals in heterocyclyloxy: three- to seven-membered saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three hetero atoms selected from a group consisting of oxygen, nitrogen and sulfur, such as oxiranyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,3-dihydrofuran-4-yl, 2,3-dihydrofuran-5-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothien-5-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 2,3-dihydropyrrol-2-yl, 2,3-dihydropyrrol-3-yl, 2,3-dihydropyrrol-4-yl, 2,3-dihydropyrrol-5-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydropyrazol-3-yl, 2,5-dihydropyrazol-4-yl, 2,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl, 2,3-dihydrothiazol-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 4,5-dihydrothiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2-morpholinyl, 3-morpholinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2-yl, 1,2,4-tetrahydrotriazin-3-yl, 1,3-dihydrooxazin-2-yl, 1,3-dithian-2-yl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 1,3-dioxolan-2-yl, 3,4,5,6-tetrahydropyridin-2-yl, 4H-1,3-thiazin-2-yl, 4H-3,1-benzothiazin-2-yl, 1,1-dioxo-2,3,4,5-tetrahydrothien-2-yl, 2H-1,4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydrooxazin-2-yl,

hetaryl, and also the hetaryl radicals in hetaryloxy: aromatic mono- or polycyclic radicals which, besides carbon ring members, may additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one sulfur atom, eg. 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4,5-tetrazin-3-yl, and also the corresponding benzo-fused derivatives.

All phenyl, hetaryl and heterocyclyl rings are preferably unsubstituted or carry one to three halogen atoms and/or one or two radicals selected from the following group: nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy and methoxycarbonyl.

With a view to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meanings, viz. in each case alone or in combination:

R¹ is nitro, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, —OR³ or —S(O)_(n)R³;

particularly preferably nitro, halogen such as, for example, fluorine, chlorine or bromine, C₁-C₆-haloalkyl, —OR³ or —SO₂R³;

R² is hydrogen, nitro, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, —OR³ or —S(O)_(n)R³;

particularly preferably hydrogen, nitro, halogen such as, for example, fluorine, chlorine or bromine, C₁-C₆-alkyl, C₁-C₆-haloalkyl, —OR³ or —SO₂R³;

n is 0, 1 or 2, particularly preferably 0 or 2;

R³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl; particularly preferably hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₃-alkenyl, C₂-C₃-alkynyl or phenyl; where the abovementioned alkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups:

hydroxyl, mercapto, amino, cyano, R³, —OR³, —SR³, —N(R³)₂, ═NOR³, —OCOR³, —SCOR³, —NR³COR³, —CO₂R³, —COSR³, —CON(R³)₂, C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl, heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted;

R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; particularly preferably hydrogen, methyl, ethyl or trifluoromethyl;

R⁵ is C₁-C₆-alkyl or C₁-C₆-haloalkyl; particularly preferably methyl, ethyl, propyl, isopropyl, butyl or isobutyl;

R⁶ is hydrogen, C₁-C₆-alkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, phenylcarbonylmethyl, or phenylsulfonyl, where the phenyl ring of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

X¹ is a straight-chain or branched C₁-C₄-alkylene, a C₂-C₄-alkenylene or a C₂-C₄-alkynylene chain, particularly preferably an ethylene, propylene, propenylene or propynylene chain which is interrupted by a hetero atom selected from the group consisting of

oxygen and sulfur, preferably oxygen,

where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups:

—OR⁷, —OCOR⁷, —OCONHR⁷ or —OSO₂R⁷;

R⁷ is hydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, phenyl, phenyl-C₁-C₄-alkyl, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may be substituted by one or more of the following radicals:

hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy;

Het is a three- to six-membered, preferably a five- or six-membered, partially or fully saturated heterocyclic group or a three- to six-membered, preferably five- or six-membered, heteroaromatic group having up to three hetero atoms, particularly preferably having one or two hetero atoms, selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

particularly preferably from the following two groups:

nitrogen or

oxygen in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R⁸;

R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals:

cyano, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy.

Particular preference is given to the compounds of the formula Ia where R¹ is bonded in position 2 and R² is bonded in position 4 of the phenyl ring.

Most particular preference is given to the compounds of the formula Ia where the substituents R¹ and R² and Q are each as defined above, X¹ is a C₁-C₃-alkylene, a C₂-C₃-alkenylene or C₂-C₃-alkynylene chain which is interrupted by an oxygen atom and

Het is a three- to six-membered, preferably a five- or six-membered, partially or fully saturated heterocyclic group or a three- to six-membered, preferably five- or six-membered, heteroaromatic group having up to three hetero atoms, particularly preferably having one or two hetero atoms, selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

particularly preferably from the following two groups:

nitrogen or

oxygen in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R⁸.

Furthermore, most particular preference is given to the compounds of the formula Ia according to the invention where the substituents R¹, R² and X¹ are each as defined above and Het is a five- or six-membered partially or fully saturated heterocyclic group or a five- or six-membered heteroaromatic group having up to three hetero atoms, particularly preferably having one or two hetero atoms, selected from the following three groups:

nitrogen,

oxygen in combination with at least one nitrogen or

sulfur in combination with at least one nitrogen,

particularly preferably from the following two groups:

nitrogen or

oxygen in combination with at least one nitrogen,

where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R⁸.

Particular preference is given to the compounds Ib of Tables 1 to 144.

TABLE A No. X¹ Het 1 OCH₂ oxiranyl 2 OCH₂ 3-methyl-2-oxiranyl 3 OCH₂ 2-oxetanyl 4 OCH₂ 3-hydroxy-3-methyl-2-oxetanyl 5 OCH₂ 3-hydroxy-3-ethyl-2-oxetanyl 6 OCH₂ 3-hydroxy-3-propyl-2-oxetanyl 7 OCH₂ 3-hydroxy-3-butyl-2-oxetanyl 8 OCH₂ 3-methoxy-3-methyl-2-oxetanyl 9 OCH₂ 3-methoxy-3-ethyl-2-oxetanyl 10 OCH₂ 3-methoxy-3-propyl-2-oxetanyl 11 OCH₂ 3-methoxy-3-butyl-2-oxetanyl 12 OCH₂ 3-trimethyl- silyloxy-3-methyl-2-oxetanyl 13 OCH₂ 3-trimethyl- silyloxy-3-ethyl-2-oxetanyl 14 OCH₂ 3-trimethyl- silyloxy-3-propyl-2-oxetanyl 15 OCH₂ 3-trimethyl- silyloxy-3-butyl-2-oxetanyl 16 OCH₂ 3-oxetanyl 17 OCH₂ 2-furyl 18 OCH₂ 4,5-dihydro-2-furyl 19 OCH₂ 2,3-dihydro-2-furyl 20 OCH₂ 3-furyl 21 OCH₂ 4,5-dihydro-3-furyl 22 OCH₂ 2,3-dihydro-3-furyl 23 OCH₂ 2-thienyl 24 OCH₂ 4,5-dihydro-2-thienyl 25 OCH₂ 2,3-dihydro-2-thienyl 26 OCH₂ 5-chloro-2-thienyl 27 OCH₂ 5-methyl-2-thienyl 28 OCH₂ 3-thienyl 29 OCH₂ 4,5-dihydro-3-thienyl 30 OCH₂ 2,3-dihydro-3-thienyl 31 OCH₂ 2-pyrrolyl 32 OCH₂ 2,5-dihydro-2-pyrrolyl 33 OCH₂ 3-pyrrolyl 34 OCH₂ 2,5-dihydro-3-pyrrolyl 35 OCH₂ 3-isoxazolyl 36 OCH₂ 4-methyl-3-isoxazolyl 37 OCH₂ 5-methyl-3-isoxazolyl 38 OCH₂ 4,5-dimethyl-3-isoxazolyl 39 OCH₂ 4,5-dihydro-3-isoxazolyl 40 OCH₂ 4-methyl-4,5-dihydro-3-isoxazolyl 41 OCH₂ 5-methyl-4,5-dihydro-3-isoxazolyl 42 OCH₂ 4,5-dimethyl-4,5-dihydro-3-isoxazo- lyl 43 OCH₂ 4-isoxazolyl 44 OCH₂ 3-methyl-4-isoxazolyl 45 OCH₂ 5-methyl-4-isoxazolyl 46 OCH₂ 5-cyclopropyl-4-isoxazolyl 47 OCH₂ 5-phenyl-4-isoxazolyl 48 OCH₂ 3,5-dimethyl-4-isoxazolyl 49 OCH₂ 4,5-dihydro-4-isoxazolyl 50 OCH₂ 3-methyl-4,5-dihydro-4-isoxazolyl 51 OCH₂ 5-methyl-4,5-dihydro-4-isoxazolyl 52 OCH₂ 3,5-dimethyl-4,5-dihydro-4-isoxazo- lyl 53 OCH₂ 5-isoxazolyl 54 OCH₂ 3-methyl-5-isoxazolyl 55 OCH₂ 4-methyl-5-isoxazolyl 56 OCH₂ 3,4-dimethyl-5-isoxazolyl 57 OCH₂ 4,5-dihydro-5-isoxazolyl 58 OCH₂ 3-methyl-4,5-dihydro-5-isoxazolyl 59 OCH₂ 4-methyl-4,5-dihydro-5-isoxazolyl 60 OCH₂ 3,4-dimethyl-4,5-dihydro-5-isoxazo- lyl 61 OCH₂ 3-isothiazolyl 62 OCH₂ 4-methyl-3-isothiazolyl 63 OCH₂ 5-methyl-3-isothiazolyl 64 OCH₂ 4-isothiazolyl 65 OCH₂ 3-methyl-4-isothiazolyl 66 OCH₂ 5-methyl-4-isothiazolyl 67 OCH₂ 5-isothiazolyl 68 OCH₂ 3-methyl-5-isothiazolyl 69 OCH₂ 4-methyl-5-isothiazolyl 70 OCH₂ 2-oxazolyl 71 OCH₂ 4-oxazolyl 72 OCH₂ 5-oxazolyl 73 OCH₂ 2-thiazolyl 74 OCH₂ 4-thiazolyl 75 OCH₂ 5-thiazolyl 76 OCH₂ 3-pyrazolyl 77 OCH₂ 4-pyrazolyl 78 OCH₂ 1-methyl-3-pyrazolyl 79 OCH₂ 1-methyl-4-pyrazolyl 80 OCH₂ 1-methyl-5-pyrazolyl 81 OCH₂ 2-imidazolyl 82 OCH₂ 1-methyl-2-imidazolyl 83 OCH₂ 5-methyl-[1,3,4]-2-oxadiazolyl 84 OCH₂ 5-methyl-[1,2,4]-3-oxadiazolyl 85 OCH₂ 5-methyl-[1,3,4]-2-thiadiazolyl 86 OCH₂ 5-methyl-[1,2,4]-3-thiadiazolyl 87 OCH₂ [1,2,4]-3-triazolyl 88 OCH₂ [1,2,3]-4-triazolyl 89 OCH₂ 2-pyridyl 90 OCH₂ 6-chloro-2-pyridyl 91 OCH₂ 6-methoxy-2-pyridyl 92 OCH₂ 6-trifluoromethyl-2-pyridyl 93 OCH₂ 3-pyridyl 94 OCH₂ 2-chloro-3-pyridyl 95 OCH₂ 2-methoxy-3-pyridyl 96 OCH₂ 4-pyridyl 97 OCH₂ 2-chloro-4-pyridyl 98 OCH₂ 2-methoxy-4-pyridyl 99 OCH₂ 2-ethoxy-4-pyridyl 100 OCH₂ 2-methylthio-4-pyridyl 101 OCH₂ 2-trifluoromethyl-5-pyridyl 102 OCH₂ 2-pyrimidinyl 103 OCH₂ 3-pyrimidinyl 104 OCH₂ 4-pyrimidinyl 105 OCH₂ 2-pyrazinyl 106 OCH₂ 3-pyridazinyl 107 OCH₂ 4-pyridazinyl 108 OCH₂ 2-(2H-1,3-oxazinyl) 109 OCH₂ 2-(6H-1,3-oxazinyl) 110 OCH₂ 4-(6H-1,3-oxazinyl) 111 OCH₂ 6-(6H-1,3-oxazinyl) 112 OCH₂ [1,3,5]-2-triazinyl 113 OCH₂ [1,2,4]-3-triazinyl 114 OCH₂ [1,2,4]-5-triazinyl 115 OCH₂ [1,2,4]-6-triazinyl 116 oxiranyl 117 3-methyl-2-oxiranyl 118 2-oxetanyl 119 3-hydroxy-3-methyl-2-oxetanyl 120 3-hydroxy-3-ethyl-2-oxetanyl 121 3-hydroxy-3-propyl-2-oxetanyl 122 3-hydroxy-3-butyl-2-oxetanyl 123 3-methoxy-3-methyl-2-oxetanyl 124 3-methoxy-3-ethyl-2-oxetanyl 125 3-methoxy-3-propyl-2-oxetanyl 126 3-methoxy-3-butyl-2-oxetanyl 127 3-trimethyl- silyloxy-3-methyl-2-oxetanyl 128 3- trimethyl- silyloxy-3-ethyl-2-oxetanyl 129 3-trimethyl- silyloxy-3-propyl-2-oxetanyl 130 3-trimethyl- silyloxy-3-butyl-2-oxetanyl 131 3-oxetanyl 132 2-furyl 133 4,5-dihydro-2-furyl 134 2,3-dihydro-2-furyl 135 3-furyl 136 4,5-dihydro-3-furyl 137 2,3-dihydro-3-furyl 138 2-thienyl 139 CH₂O 4,5-dihydro-2-thienyl 140 CH₂O 2,3-dihydro-2-thienyl 141 CH₂O 5-chloro-2-thienyl 142 CH₂O 5-methyl-2-thienyl 143 CH₂O 3-thienyl 144 CH₂O 4,5-dihydro-3-thienyl 145 CH₂O 2,3-dihydro-3-thienyl 146 CH₂O 2-pyrrolyl 147 CH₂O 2,5-dihydro-2-pyrrolyl 148 CH₂O 3-pyrrolyl 149 CH₂O 2,5-dihydro-3-pyrrolyl 150 CH₂O 3-isoxazolyl 151 CH₂O 4-methyl-3-isoxazolyl 152 CH₂O 5-methyl-3-isoxazolyl 153 CH₂O 4,5-dimethyl-3-isoxazolyl 154 CH₂O 4,5-dihydro-3-isoxazolyl 155 CH₂O 4-methyl-4,5-dihydro-3-isoxazolyl 156 CH₂O 5-methyl-4,5-dihydro-3-isoxazolyl 157 CH₂O 4,5-dimethyl-4,5-dihydro-3-isoxazo- lyl 158 CH₂O 4-isoxazolyl 159 CH₂O 3-methyl-4-isoxazolyl 160 CH₂O 5-methyl-4-isoxazolyl 161 CH₂O 5-cyclopropyl-4-isoxazolyl 162 CH₂O 5-phenyl-4-isoxazolyl 163 CH₂O 3,5-dimethyl-4-isoxazolyl 164 CH₂O 4,5-dihydro-4-isoxazolyl 165 CH₂O 3-methyl-4,5-dihydro-4-isoxazolyl 166 CH₂O 5-methyl-4,5-dihydro-4-isoxazolyl 167 CH₂O 3,5-dimethyl-4,5-dihydro-4-isoxazo- lyl 168 CH₂O 5-isoxazolyl 169 CH₂O 3-methyl-5-isoxazolyl 170 CH₂O 4-methyl-5-isoxazolyl 171 CH₂O 3,4-dimethyl-5-isoxazolyl 172 CH₂O 4,5-dihydro-5-isoxazolyl 173 CH₂O 3-methyl-4,5-dihydro-5-isoxazolyl 174 CH₂O 4-methyl-4,5-dihydro-5-isoxazolyl 175 CH₂O 3,4-dimethyl-4,5-dihydro-5-isoxazo- lyl 176 CH₂O 3-isothiazolyl 177 CH₂O 4-methyl-3-isothiazolyl 178 CH₂O 5-methyl-3-isothiazolyl 179 CH₂O 4-isothiazolyl 180 CH₂O 3-methyl-4-isothiazolyl 181 CH₂O 5-methyl-4-isothiazolyl 182 CH₂O 5-isothiazolyl 183 CH₂O 3-methyl-5-isothiazolyl 184 CH₂O 4-methyl-5-isothiazolyl 185 CH₂O 2-oxazolyl 186 CH₂O 4-oxazolyl 187 CH₂O 5-oxazolyl 188 CH₂O 2-thiazolyl 189 CH₂O 4-thiazolyl 190 CH₂O 5-thiazolyl 191 CH₂O 3-pyrazolyl 192 CH₂O 4-pyrazolyl 193 CH₂O 1-methyl-3-pyrazolyl 194 CH₂O 1-methyl-4-pyrazolyl 195 CH₂O 1-methyl-5-pyrazolyl 196 CH₂O 2-imidazolyl 197 CH₂O 1-methyl-2-imidazolyl 198 CH₂O 5-methyl-[1,3,4]-2-oxadiazolyl 199 CH₂O 5-methyl-[1,2,4]-3-oxadiazolyl 200 CH₂O 5-methyl-[1,3,4]-2-thiadiazolyl 201 CH₂O 5-methyl-[1,2,4]-3-thiadiazolyl 202 CH₂O [1,2,4]-3-triazolyl 203 CH₂O [1,2,3]-4-triazolyl 204 CH₂O 2-pyridyl 205 CH₂O 6-chloro-2-pyridyl 206 CH₂O 6-methoxy-2-pyridyl 207 CH₂O 6-trifluoromethyl-2-pyridyl 208 CH₂O 3-pyridyl 209 CH₂O 2-chloro-3-pyridyl 210 CH₂O 2-methoxy-3-pyridyl 211 CH₂O 4-pyridyl 212 CH₂O 2-chloro-4-pyridyl 213 CH₂O 2-methoxy-4-pyridyl 214 CH₂O 2-ethoxy-4-pyridyl 215 CH₂O 2-methylthio-4-pyridyl 216 CH₂O 2-trifluoromethyl-5-pyridyl 217 CH₂O 2-pyrimidinyl 218 CH₂O 3-pyrimidinyl 219 CH₂O 4-pyrimidinyl 220 CH₂O 2-pyrazinyl 221 CH₂O 3-pyridazinyl 222 CH₂O 4-pyridazinyl 223 CH₂O 2-(2H-1,3-oxazinyl) 224 CH₂O 2-(6H-1,3-oxazinyl) 225 CH₂O 4-(6H-1,3-oxazinyl) 226 CH₂O 6-(6H-1,3-oxazinyl) 227 CH₂O [1,3,5]-2-triazinyl 228 CH₂O [1,2,4]-3-triazinyl 229 CH₂O [1,2,4]-5-triazinyl 230 CH₂O [1,2,4]-6-triazinyl 231 OCH₂CH₂ oxiranyl 232 OCH₂CH₂ 3-methyl-2-oxiranyl 233 OCH₂CH₂ 2-oxetanyl 234 OCH₂CH₂ 3-hydroxy-3-methyl-2-oxetanyl 235 OCH₂CH₂ 3-hydroxy-3-ethyl-2-oxetanyl 236 OCH₂CH₂ 3-hydroxy-3-propyl-2-oxetanyl 237 OCH₂CH₂ 3-hydroxy-3-butyl-2-oxetanyl 238 OCH₂CH₂ 3-methoxy-3-methyl-2-oxetanyl 239 OCH₂CH₂ 3-methoxy-3-ethyl-2-oxetanyl 240 OCH₂CH₂ 3-methoxy-3-propyl-2-oxetanyl 241 OCH₂CH₂ 3-methoxy-3-butyl-2-oxetanyl 242 OCH₂CH₂ 3-trimethyl- silyloxy-3-methyl-2-oxetanyl 243 OCH₂CH₂ 3-trimethyl- silyloxy-3-ethyl-2-oxetanyl 244 OCH₂CH₂ 3-trimethyl- silyloxy-3-propyl-2-oxetanyl 245 OCH₂CH₂ 3-trimethyl- silyloxy-3-butyl-2-oxetanyl 246 OCH₂CH₂ 3-oxetanyl 247 OCH₂CH₂ 2-furyl 248 OCH₂CH₂ 4,5-dihydro-2-furyl 249 OCH₂CH₂ 2,3-dihydro-2-furyl 250 OCH₂CH₂ 3-furyl 251 OCH₂CH₂ 4,5-dihydro-3-furyl 252 OCH₂CH₂ 2,3-dihydro-3-furyl 253 OCH₂CH₂ 2-thienyl 254 OCH₂CH₂ 4,5-dihydro-2-thienyl 255 OCH₂CH₂ 2,3-dihydro-2-thienyl 256 OCH₂CH₂ 5-chloro-2-thienyl 257 OCH₂CH₂ 5-methyl-2-thienyl 258 OCH₂CH₂ 3-thienyl 259 OCH₂CH₂ 4,5-dihydro-3-thienyl 260 OCH₂CH₂ 2,3-dihydro-3-thienyl 261 OCH₂CH₂ 2-pyrrolyl 262 OCH₂CH₂ 2,5-dihydro-2-pyrrolyl 263 OCH₂CH₂ 3-pyrrolyl 264 OCH₂CH₂ 2,5-dihydro-3-pyrrolyl 265 OCH₂CH₂ 3-isoxazolyl 266 OCH₂CH₂ 4-methyl-3-isoxazolyl 267 OCH₂CH₂ 5-methyl-3-isoxazolyl 268 OCH₂CH₂ 4,5-dimethyl-3-isoxazolyl 269 OCH₂CH₂ 4,5-dihydro-3-isoxazolyl 270 OCH₂CH₂ 4-methyl-4,5-dihydro-3-isoxazolyl 271 OCH₂CH₂ 5-methyl-4,5-dihydro-3-isoxazolyl 272 OCH₂CH₂ 4,5-dimethyl-4,5-dihydro-3-isoxazo- lyl 273 OCH₂CH₂ 4-isoxazolyl 274 OCH₂CH₂ 3-methyl-4-isoxazolyl 275 OCH₂CH₂ 5-methyl-4-isoxazolyl 276 OCH₂CH₂ 5-cyclopropyl-4-isoxazolyl 277 OCH₂CH₂ 5-phenyl-4-isoxazolyl 278 OCH₂CH₂ 3,5-dimethyl-4-isoxazolyl 279 OCH₂CH₂ 4,5-dihydro-4-isoxazolyl 280 OCH₂CH₂ 3-methyl-4,5-dihydro-4-isoxazolyl 281 OCH₂CH₂ 5-methyl-4,5-dihydro-4-isoxazolyl 282 OCH₂CH₂ 3,5-dimethyl-4,5-dihydro-4-isoxazo- lyl 283 OCH₂CH₂ 5-isoxazolyl 284 OCH₂CH₂ 3-methyl-5-isoxazolyl 285 OCH₂CH₂ 4-methyl-5-isoxazolyl 286 OCH₂CH₂ 3,4-dimethyl-5-isoxazolyl 287 OCH₂CH₂ 4,5-dihydro-5-isoxazolyl 288 OCH₂CH₂ 3-methyl-4,5-dihydro-5-isoxazolyl 289 OCH₂CH₂ 4-methyl-4,5-dihydro-5-isoxazolyl 290 OCH₂CH₂ 3,4-dimethyl-4,5-dihydro-5-isoxazo- lyl 291 OCH₂CH₂ 3-isothiazolyl 292 OCH₂CH₂ 4-methyl-3-isothiazolyl 293 OCH₂CH₂ 5-methyl-3-isothiazolyl 294 OCH₂CH₂ 4-isothiazolyl 295 OCH₂CH₂ 3-methyl-4-isothiazolyl 296 OCH₂CH₂ 5-methyl-4-isothiazolyl 297 OCH₂CH₂ 5-isothiazolyl 298 OCH₂CH₂ 3-methyl-5-isothiazolyl 299 OCH₂CH₂ 4-methyl-5-isothiazolyl 300 OCH₂CH₂ 2-oxazolyl 301 OCH₂CH₂ 4-oxazolyl 302 OCH₂CH₂ 5-oxazolyl 303 OCH₂CH₂ 2-thiazolyl 304 OCH₂CH₂ 4-thiazolyl 305 OCH₂CH₂ 5-thiazolyl 306 OCH₂CH₂ 3-pyrazolyl 307 OCH₂CH₂ 4-pyrazolyl 308 OCH₂CH₂ 1-methyl-3-pyrazolyl 309 OCH₂CH₂ 1-methyl-4-pyrazolyl 310 OCH₂CH₂ 1-methyl-5-pyrazolyl 311 OCH₂CH₂ 2-imidazolyl 312 OCH₂CH₂ 1-methyl-2-imidazolyl 313 OCH₂CH₂ 5-methyl-[1,3,4]-2-oxadiazolyl 314 OCH₂CH₂ 5-methyl-[1,2,4]-3-oxadiazolyl 315 OCH₂CH₂ 5-methyl-[1,3,4]-2-thiadiazolyl 316 OCH₂CH₂ 5-methyl-[1,2,4]-3-thiadiazolyl 317 OCH₂CH₂ [1,2,4]-3-triazolyl 318 OCH₂CH₂ [1,2,3]-4-triazolyl 319 OCH₂CH₂ 2-pyridyl 320 OCH₂CH₂ 6-chloro-2-pyridyl 321 OCH₂CH₂ 6-methoxy-2-pyridyl 322 OCH₂CH₂ 6-trifluoromethyl-2-pyridyl 323 OCH₂CH₂ 3-pyridyl 324 OCH₂CH₂ 2-chloro-3-pyridyl 325 OCH₂CH₂ 2-methoxy-3-pyridyl 326 OCH₂CH₂ 4-pyridyl 327 OCH₂CH₂ 2-chloro-4-pyridyl 328 OCH₂CH₂ 2-methoxy-4-pyridyl 329 OCH₂CH₂ 2-ethoxy-4-pyridyl 330 OCH₂CH₂ 2-methylthio-4-pyridyl 331 OCH₂CH₂ 2-trifluoromethyl-5-pyridyl 332 OCH₂CH₂ 2-pyrimidinyl 333 OCH₂CH₂ 3-pyrimidinyl 334 OCH₂CH₂ 4-pyrimidinyl 335 OCH₂CH₂ 2-pyrazinyl 336 OCH₂CH₂ 3-pyridazinyl 337 OCH₂CH₂ 4-pyridazinyl 338 OCH₂CH₂ 2-(2H-1,3-oxazinyl) 339 OCH₂CH₂ 2-(6H-1,3-oxazinyl) 340 OCH₂CH₂ 4-(6H-1,3-oxazinyl) 341 OCH₂CH₂ 6-(6H-1,3-oxazinyl) 342 OCH₂CH₂ [1,3,5]-2-triazinyl 343 OCH₂CH₂ [1,2,4]-3-triazinyl 344 OCH₂CH₂ [1,2,4]-5-triazinyl 345 OCH₂CH₂ [1,2,4]-6-triazinyl 346 CH₂CH₂O oxiranyl 347 CH₂CH₂O 3-methyl-2-oxiranyl 348 CH₂CH₂O 2-oxetanyl 349 CH₂CH₂O 3-hydroxy-3-methyl-2-oxetanyl 350 CH₂CH₂O 3-hydroxy-3-ethyl-2-oxetanyl 351 CH₂CH₂O 3-hydroxy-3-propyl-2-oxetanyl 352 CH₂CH₂O 3-hydroxy-3-butyl-2-oxetanyl 353 CH₂CH₂O 3-methoxy-3-methyl-2-oxetanyl 354 CH₂CH₂O 3-methoxy-3-ethyl-2-oxetanyl 355 CH₂CH₂O 3-methoxy-3-propyl-2-oxetanyl 356 CH₂CH₂O 3-methoxy-3-butyl-2-oxetanyl 357 CH₂CH₂O 3-trimethyl- silyloxy-3-methyl-2-oxetanyl 358 CH₂CH₂O 3-trimethyl- silyloxy-3-ethyl-2-oxetanyl 359 CH₂CH₂O 3-trimethyl- silyloxy-3-propyl-2-oxetanyl 360 CH₂CH₂O 3-trimethyl- silyloxy-3-butyl-2-oxetanyl 361 CH₂CH₂O 3-oxetanyl 362 CH₂CH₂O 2-furyl 363 CH₂CH₂O 4,5-dihydro-2-furyl 364 CH₂CH₂O 2,3-dihydro-2-furyl 365 CH₂CH₂O 3-furyl 366 CH₂CH₂O 4,5-dihydro-3-furyl 367 CH₂CH₂O 2,3-dihydro-3-furyl 368 CH₂CH₂O 2-thienyl 369 CH₂CH₂O 4,5-dihydro-2-thienyl 370 CH₂CH₂O 2,3-dihydro-2-thienyl 371 CH₂CH₂O 5-chloro-2-thienyl 372 CH₂CH₂O 5-methyl-2-thienyl 373 CH₂CH₂O 3-thienyl 374 CH₂CH₂O 4,5-dihydro-3-thienyl 375 CH₂CH₂O 2,3-dihydro-3-thienyl 376 CH₂CH₂O 2-pyrrolyl 377 CH₂CH₂O 2,5-dihydro-2-pyrrolyl 378 CH₂CH₂O 3-pyrrolyl 379 CH₂CH₂O 2,5-dihydro-3-pyrrolyl 380 CH₂CH₂O 3-isoxazolyl 381 CH₂CH₂O 4-methyl-3-isoxazolyl 382 CH₂CH₂O 5-methyl-3-isoxazolyl 383 CH₂CH₂O 4,5-dimethyl-3-isoxazolyl 384 CH₂CH₂O 4,5-dihydro-3-isoxazolyl 385 CH₂CH₂O 4-methyl-4,5-dihydro-3-isoxazolyl 386 CH₂CH₂O 5-methyl-4,5-dihydro-3-isoxazolyl 387 CH₂CH₂O 4,5-dimethyl-4,5-dihydro-3-isoxazo- lyl 388 CH₂CH₂O 4-isoxazolyl 389 CH₂CH₂O 3-methyl-4-isoxazolyl 390 CH₂CH₂O 5-methyl-4-isoxazolyl 391 CH₂CH₂O 5-cyclopropyl-4-isoxazolyl 392 CH₂CH₂O 5-phenyl-4-isoxazolyl 393 CH₂CH₂O 3,5-dimethyl-4-isoxazolyl 394 CH₂CH₂O 4,5-dihydro-4-isoxazolyl 395 CH₂CH₂O 3-methyl-4,5-dihydro-4-isoxazolyl 396 CH₂CH₂O 5-methyl-4,5-dihydro-4-isoxazolyl 397 CH₂CH₂O 3,5-dimethyl-4,5-dihydro-4-isoxazo- lyl 398 CH₂CH₂O 5-isoxazolyl 399 CH₂CH₂O 3-methyl-5-isoxazolyl 400 CH₂CH₂O 4-methyl-5-isoxazolyl 401 CH₂CH₂O 3,4-dimethyl-5-isoxazolyl 402 CH₂CH₂O 4,5-dihydro-5-isoxazolyl 403 CH₂CH₂O 3-methyl-4,5-dihydro-5-isoxazolyl 404 CH₂CH₂O 4-methyl-4,5-dihydro-5-isoxazolyl 405 CH₂CH₂O 3,4-dimethyl-4,5-dihydro-5-isoxazo- lyl 406 CH₂CH₂O 3-isothiazolyl 407 CH₂CH₂O 4-methyl-3-isothiazolyl 408 CH₂CH₂O 5-methyl-3-isothiazolyl 409 CH₂CH₂O 4-isothiazolyl 410 CH₂CH₂O 3-methyl-4-isothiazolyl 411 CH₂CH₂O 5-methyl-4-isothiazolyl 412 CH₂CH₂O 5-isothiazolyl 413 CH₂CH₂O 3-methyl-5-isothiazolyl 414 CH₂CH₂O 4-methyl-5-isothiazolyl 415 CH₂CH₂O 2-oxazolyl 416 CH₂CH₂O 4-oxazolyl 417 CH₂CH₂O 5-oxazolyl 418 CH₂CH₂O 2-thiazolyl 419 CH₂CH₂O 4-thiazolyl 420 CH₂CH₂O 5-thiazolyl 421 CH₂CH₂O 3-pyrazolyl 422 CH₂CH₂O 4-pyrazolyl 423 CH₂CH₂O 1-methyl-3-pyrazolyl 424 CH₂CH₂O 1-methyl-4-pyrazolyl 425 CH₂CH₂O 1-methyl-5-pyrazolyl 426 CH₂CH₂O 2-imidazolyl 427 CH₂CH₂O 1-methyl-2-imidazolyl 428 CH₂CH₂O 5-methyl-[1,3,4]-2-oxadiazolyl 429 CH₂CH₂O 5-methyl-[1,2,4]-3-oxadiazolyl 430 CH₂CH₂O 5-methyl-[1,3,4]-2-thiadiazolyl 431 CH₂CH₂O 5-methyl-[1,2,4]-3-thiadiazolyl 432 CH₂CH₂O [1,2,4]-3-triazolyl 433 CH₂CH₂O [1,2,3]-4-triazolyl 434 CH₂CH₂O 2-pyridyl 435 CH₂CH₂O 6-chloro-2-pyridyl 436 CH₂CH₂O 6-methoxy-2-pyridyl 437 CH₂CH₂O 6-trifiuoromethyl-2-pyridyl 438 CH₂CH₂O 3-pyridyl 439 CH₂CH₂O 2-chloro-3-pyridyl 440 CH₂CH₂O 2-methoxy-3-pyridyl 441 CH₂CH₂O 4-pyridyl 442 CH₂CH₂O 2-chloro-4-pyridyl 443 CH₂CH₂O 2-methoxy-4-pyridyl 444 CH₂CH₂O 2-ethoxy-4-pyridyl 445 CH₂CH₂O 2-methylthio-4-pyridyl 446 CH₂CH₂O 2-trifiuoromethyl-5-pyridyl 447 CH₂CH₂O 2-pyrimidinyl 448 CH₂CH₂O 3-pyrimidinyl 449 CH₂CH₂O 4-pyrimidinyl 450 CH₂CH₂O 2-pyrazinyl 451 CH₂CH₂O 3-pyridazinyl 452 CH₂CH₂O 4-pyridazinyl 453 CH₂CH₂O 2-(2H-1,3-oxazinyl) 454 CH₂CH₂O 2-(6H-1,3-oxazinyl) 455 CH₂CH₂O 4-(6H-1,3-oxazinyl) 456 CH₂CH₂O 6-(6H-1,3-oxazinyl) 457 CH₂CH₂O [1,3,5]-2-triazinyl 458 CH₂CH₂O [1,2,4]-3-triazinyl 459 CH₂CH₂O [1,2,4]-5-triazinyl 460 CH₂CH₂O [1,2,4]-6-triazinyl 461 CH₂OCH₂ oxiranyl 462 CH₂OCH₂ 3-methyl-2-oxiranyl 463 CH₂OCH₂ 2-oxetanyl 464 CH₂OCH₂ 3-hydroxy-3-methyl-2-oxetanyl 465 CH₂OCH₂ 3-hydroxy-3-ethyl-2-oxetanyl 466 CH₂OCH₂ 3-hydroxy-3-propyl-2-oxetanyl 467 CH₂OCH₂ 3-hydroxy-3-butyl-2-oxetanyl 468 CH₂OCH₂ 3-methoxy-3-methyl-2-oxetanyl 469 CH₂OCH₂ 3-methoxy-3-ethyl-2-oxetanyl 470 CH₂OCH₂ 3-methoxy-3-propyl-2-oxetanyl 471 CH₂OCH₂ 3-methoxy-3-butyl-2-oxetanyl 472 CH₂OCH₂ 3-trimethyl- silyloxy-3-methyl-2-oxetanyl 473 CH₂OCH₂ 3-trimethyl- silyloxy-3-ethyl-2-oxetanyl 474 CH₂OCH₂ 3-trimethyl- silyloxy-3-propyl-2-oxetanyl 475 CH₂OCH₂ 3-trimethyl- silyloxy-3-butyl-2-oxetanyl 476 CH₂OCH₂ 3-oxetanyl 477 CH₂OCH₂ 2-furyl 478 CH₂OCH₂ 4,5-dihydro-2-furyl 479 CH₂OCH₂ 2,3-dihydro-2-furyl 480 CH₂OCH₂ 3-furyl 481 CH₂OCH₂ 4,5-dihydro-3-furyl 482 CH₂OCH₂ 2,3-dihydro-3-furyl 483 CH₂OCH₂ 2-thienyl 484 CH₂OCH₂ 4,5-dihydro-2-thienyl 485 CH₂OCH₂ 2,3-dihydro-2-thienyl 486 CH₂OCH₂ 5-chloro-2-thienyl 487 CH₂OCH₂ 5-methyl-2-thienyl 488 CH₂OCH₂ 3-thienyl 489 CH₂OCH₂ 4,5-dihydro-3-thienyl 490 CH₂OCH₂ 2,3-dihydro-3-thienyl 491 CH₂OCH₂ 2-pyrrolyl 492 CH₂OCH₂ 2,5-dihydro-2-pyrrolyl 493 CH₂OCH₂ 3-pyrrolyl 494 CH₂OCH₂ 2,5-dihydro-3-pyrrolyl 495 CH₂OCH₂ 3-isoxazolyl 496 CH₂OCH₂ 4-methyl-3-isoxazolyl 497 CH₂OCH₂ 5-methyl-3-isoxazolyl 498 CH₂OCH₂ 4,5-dimethyl-3-isoxazolyl 499 CH₂OCH₂ 4,5-dihydro-3-isoxazolyl 500 CH₂OCH₂ 4-methyl-4,5-dihydro-3-isoxazolyl 501 CH₂OCH₂ 5-methyl-4,5-dihydro-3-isoxazolyl 502 CH₂OCH₂ 4,5-dimethyl-4,5-dihydro-3-isoxazo- lyl 503 CH₂OCH₂ 4-isoxazolyl 504 CH₂OCH₂ 3-methyl-4-isoxazolyl 505 CH₂OCH₂ 5-methyl-4-isoxazolyl 506 CH₂OCH₂ 5-cyclopropyl-4-isoxazolyl 507 CH₂OCH₂ 5-phenyl-4-isoxazolyl 508 CH₂OCH₂ 3,5-dimethyl-4-isoxazolyl 509 CH₂OCH₂ 4,5-dihydro-4-isoxazolyl 510 CH₂OCH₂ 3-methyl-4,5-dihydro-4-isoxazolyl 511 CH₂OCH₂ 5-methyl-4,5-dihydro-4-isoxazolyl 512 CH₂OCH₂ 3,5-dimethyl-4,5-dihydro-4-isoxazo- lyl 513 CH₂OCH₂ 5-isoxazolyl 514 CH₂OCH₂ 3-methyl-5-isoxazolyl 515 CH₂OCH₂ 4-methyl-5-isoxazolyl 516 CH₂OCH₂ 3,4-dimethyl-5-isoxazolyl 517 CH₂OCH₂ 4,5-dihydro-5-isoxazolyl 518 CH₂OCH₂ 3-methyl-4,5-dihydro-5-isoxazolyl 519 CH₂OCH₂ 4-methyl-4,5-dihydro-5-isoxazolyl 520 CH₂OCH₂ 3,4-dimethyl-4,5-dihydro-5-isoxazo- lyl 521 CH₂OCH₂ 3-isothiazolyl 522 CH₂OCH₂ 4-methyl-3-isothiazolyl 523 CH₂OCH₂ 5-methyl-3-isothiazolyl 524 CH₂OCH₂ 4-isothiazolyl 525 CH₂OCH₂ 3-methyl-4-isothiazolyl 526 CH₂OCH₂ 5-methyl-4-isothiazolyl 527 CH₂OCH₂ 5-isothiazolyl 528 CH₂OCH₂ 3-methyl-5-isothiazolyl 529 CH₂OCH₂ 4-methyl-5-isothiazolyl 530 CH₂OCH₂ 2-oxazolyl 531 CH₂OCH₂ 4-oxazolyl 532 CH₂OCH₂ 5-oxazolyl 533 CH₂OCH₂ 2-thiazolyl 534 CH₂OCH₂ 4-thiazolyl 535 CH₂OCH₂ 5-thiazolyl 536 CH₂OCH₂ 3-pyrazolyl 537 CH₂OCH₂ 4-pyrazolyl 538 CH₂OCH₂ 1-methyl-3-pyrazolyl 539 CH₂OCH₂ 1-methyl-4-pyrazolyl 540 CH₂OCH₂ 1-methyl-5-pyrazolyl 541 CH₂OCH₂ 2-imidazolyl 542 CH₂OCH₂ 1-methyl-2-imidazolyl 543 CH₂OCH₂ 5-methyl-[1,3,4]-2-oxadiazolyl 544 CH₂OCH₂ 5-methyl-[1,2,4]-3-oxadiazolyl 545 CH₂OCH₂ 5-methyl-[1,3,4]-2-thiadiazolyl 546 CH₂OCH₂ 5-methyl-[1,2,4]-3-thiadiazolyl 547 CH₂OCH₂ [1,2,4]-3-triazolyl 548 CH₂OCH₂ [1,2,3]-4-triazolyl 549 CH₂OCH₂ 2-pyridyl 550 CH₂OCH₂ 6-chloro-2-pyridyl 551 CH₂OCH₂ 6-methoxy-2-pyridyl 552 CH₂OCH₂ 6-trifluoromethyl-2-pyridyl 553 CH₂OCH₂ 3-pyridyl 554 CH₂OCH₂ 2-chloro-3-pyridyl 555 CH₂OCH₂ 2-methoxy-3-pyridyl 556 CH₂OCH₂ 4-pyridyl 557 CH₂OCH₂ 2-chloro-4-pyridyl 558 CH₂OCH₂ 2-methoxy-4-pyridyl 559 CH₂OCH₂ 2-ethoxy-4-pyridyl 560 CH₂OCH₂ 2-methylthio-4-pyridyl 561 CH₂OCH₂ 2-trifluoromethyl-5-pyridyl 562 CH₂OCH₂ 2-pyrimidinyl 563 CH₂OCH₂ 3-pyrimidinyl 564 CH₂OCH₂ 4-pyrimidinyl 565 CH₂OCH₂ 2-pyrazinyl 566 CH₂OCH₂ 3-pyridazinyl 567 CH₂OCH₂ 4-pyridazinyl 568 CH₂OCH₂ 2-(2H-1,3-oxazinyl) 569 CH₂OCH₂ 2-(6H-1,3-oxazinyl) 570 CH₂OCH₂ 4-(6H-1,3-oxazinyl) 571 CH₂OCH₂ 6-(6H-1,3-oxazinyl) 572 CH₂OCH₂ [1,3,5]-2-triazinyl 573 CH₂OCH₂ [1,2,4]-3-triazinyl 574 CH₂OCH₂ [1,2,4]-5-triazinyl 575 CH₂OCH₂ [1,2,4]-6-triazinyl 576 CH₂OCH₂CH═CH oxiranyl 577 CH₂OCH₂CH═CH 3-methyl-2-oxiranyl 578 CH₂OCH₂CH═CH 2-oxetanyl 579 CH₂OCH₂CH═CH 3-hydroxy-3-methyl-2-oxetanyl 580 CH₂OCH₂CH═CH 3-hydroxy-3-ethyl-2-oxetanyl 581 CH₂OCH₂CH═CH 3-hydroxy-3-propyl-2-oxetanyl 582 CH₂OCH₂CH═CH 3-hydroxy-3-butyl-2-oxetanyl 583 CH₂OCH₂CH═CH 3-methoxy-3-methyl-2-oxetanyl 584 CH₂OCH₂CH═CH 3-methoxy-3-ethyl-2-oxetanyl 585 CH₂OCH₂CH═CH 3-methoxy-3-propyl-2-oxetanyl 586 CH₂OCH₂CH═CH 3-methoxy-3-butyl-2-oxetanyl 587 CH₂OCH₂CH═CH 3-trimethyl- silyloxy-3-methyl-2-oxetanyl 588 CH₂OCH₂CH═CH 3-trimethyl- silyloxy-3-ethyl-2-oxetanyl 589 CH₂OCH₂CH═CH 3-trimethyl- silyloxy-3-propyl-2-oxetanyl 590 CH₂OCH₂CH═CH 3-trimethyl- silyloxy-3-butyl-2-oxetanyl 591 CH₂OCH₂CH═CH 3-oxetanyl 592 CH₂OCH₂CH═CH 2-furyl 593 CH₂OCH₂CH═CH 4,5-dihydro-2-furyl 594 CH₂OCH₂CH═CH 2,3-dihydro-2-furyl 595 CH₂OCH₂CH═CH 3-furyl 596 CH₂OCH₂CH═CH 4,5-dihydro-3-furyl 597 CH₂OCH₂CH═CH 2,3-dihydro-3-furyl 598 CH₂OCH₂CH═CH 2-thienyl 599 CH₂OCH₂CH═CH 4,5-dihydro-2-thienyl 600 CH₂OCH₂CH═CH 2,3-dihydro-2-thienyl 601 CH₂OCH₂CH═CH 5-chloro-2-thienyl 602 CH₂OCH₂CH═CH 5-methyl-2-thienyl 603 CH₂OCH₂CH═CH 3-thienyl 604 CH₂OCH₂CH═CH 4,5-dihydro-3-thienyl 605 CH₂OCH₂CH═CH 2,3-dihydro-3-thienyl 606 CH₂OCH₂CH═CH 2-pyrrolyl 607 CH₂OCH₂CH═CH 2,5-dihydro-2-pyrrolyl 608 CH₂OCH₂CH═CH 3-pyrrolyl 609 CH₂OCH₂CH═CH 2,5-dihydro-3-pyrrolyl 610 CH₂OCH₂CH═CH 3-isoxazolyl 611 CH₂OCH₂CH═CH 4-methyl-3-isoxazolyl 612 CH₂OCH₂CH═CH 5-methyl-3-isoxazolyl 613 CH₂OCH₂CH═CH 4,5-dimethyl-3-isoxazolyl 614 CH₂OCH₂CH═CH 4,5-dihydro-3-isoxazolyl 615 CH₂OCH₂CH═CH 4-methyl-4,5-dihydro-3-isoxazolyl 616 CH₂OCH₂CH═CH 5-methyl-4,5-dihydro-3-isoxazolyl 617 CH₂OCH₂CH═CH 4,5-dimethyl-4,5-dihydro-3-isoxazo- lyl 618 CH₂OCH₂CH═CH 4-isoxazolyl 619 CH₂OCH₂CH═CH 3-methyl-4-isoxazolyl 620 CH₂OCH₂CH═CH 5-methyl-4-isoxazolyl 621 CH₂OCH₂CH═CH 5-cyclopropyl-4-isoxazolyl 622 CH₂OCH₂CH═CH 5-phenyl-4-isoxazolyl 623 CH₂OCH₂CH═CH 3,5-dimethyl-4-isoxazolyl 624 CH₂OCH₂CH═CH 4,5-dihydro-4-isoxazolyl 625 CH₂OCH₂CH═CH 3-methyl-4,5-dihydro-4-isoxazolyl 626 CH₂OCH₂CH═CH 5-methyl-4,5-dihydro-4-isoxazolyl 627 CH₂OCH₂CH═CH 3,5-dimethyl-4,5-dihydro-4-isoxazo- lyl 628 CH₂OCH₂CH═CH 5-isoxazolyl 629 CH₂OCH₂CH═CH 3-methyl-5-isoxazolyl 630 CH₂OCH₂CH═CH 4-methyl-5-isoxazolyl 631 CH₂OCH₂CH═CH 3,4-dimethyl-5-isoxazolyl 632 CH₂OCH₂CH═CH 4,5-dihydro-5-isoxazolyl 633 CH₂OCH₂CH═CH 3-methyl-4,5-dihydro-5-isoxazolyl 634 CH₂OCH₂CH═CH 4-methyl-4,5-dihydro-5-isoxazolyl 635 CH₂OCH₂CH═CH 3,4-dimethyl-4,5-dihydro-5-isoxazo- lyl 636 CH₂OCH₂CH═CH 3-isothiazolyl 637 CH₂OCH₂CH═CH 4-methyl-3-isothiazolyl 638 CH₂OCH₂CH═CH 5-methyl-3-isothiazolyl 639 CH₂OCH₂CH═CH 4-isothiazolyl 640 CH₂OCH₂CH═CH 3-methyl-4-isothiazolyl 641 CH₂OCH₂CH═CH 5-methyl-4-isothiazolyl 642 CH₂OCH₂CH═CH 5-isothiazolyl 643 CH₂OCH₂CH═CH 3-methyl-5-isothiazolyl 644 CH₂OCH₂CH═CH 4-methyl-5-isothiazolyl 645 CH₂OCH₂CH═CH 2-oxazolyl 646 CH₂OCH₂CH═CH 4-oxazolyl 647 CH₂OCH₂CH═CH 5-oxazolyl 648 CH₂OCH₂CH═CH 2-thiazolyl 649 CH₂OCH₂CH═CH 4-thiazolyl 650 CH₂OCH₂CH═CH 5-thiazolyl 651 CH₂OCH₂CH═CH 3-pyrazolyl 652 CH₂OCH₂CH═CH 4-pyrazolyl 653 CH₂OCH₂CH═CH 1-methyl-3-pyrazolyl 654 CH₂OCH₂CH═CH 1-methyl-4-pyrazolyl 655 CH₂OCH₂CH═CH 1-methyl-5-pyrazolyl 656 CH₂OCH₂CH═CH 2-imidazolyl 657 CH₂OCH₂CH═CH 1-methyl-2-imidazolyl 658 CH₂OCH₂CH═CH 5-methyl-[1,3,4]-2-oxadiazolyl 659 CH₂OCH₂CH═CH 5-methyl-[1,2,4]-3-oxadiazolyl 660 CH₂OCH₂CH═CH 5-methyl-[1,3,4]-2-thiadiazolyl 661 CH₂OCH₂CH═CH 5-methyl-[1,2,4]-3-thiadiazolyl 662 CH₂OCH₂CH═CH [1,2,4]-3-triazolyl 663 CH₂OCH₂CH═CH [1,2,3]-4-triazolyl 664 CH₂OCH₂CH═CH 2-pyridyl 665 CH₂OCH₂CH═CH 6-chloro-2-pyridyl 666 CH₂OCH₂CH═CH 6-methoxy-2-pyridyl 667 CH₂OCH₂CH═CH 6-trifluoromethyl-2-pyridyl 668 CH₂OCH₂CH═CH 3-pyridyl 669 CH₂OCH₂CH═CH 2-chloro-3-pyridyl 670 CH₂OCH₂CH═CH 2-methoxy-3-pyridyl 671 CH₂OCH₂CH═CH 4-pyridyl 672 CH₂OCH₂CH═CH 2-chloro-4-pyridyl 673 CH₂OCH₂CH═CH 2-methoxy-4-pyridyl 674 CH₂OCH₂CH═CH 2-ethoxy-4-pyridyl 675 CH₂OCH₂CH═CH 2-methylthio-4-pyridyl 676 CH₂OCH₂CH═CH 2-trifluoromethyl-5-pyridyl 677 CH₂OCH₂CH═CH 2-pyrimidinyl 678 CH₂OCH₂CH═CH 3-pyrimidinyl 679 CH₂OCH₂CH═CH 4-pyrimidinyl 680 CH₂OCH₂CH═CH 2-pyrazinyl 681 CH₂OCH₂CH═CH 3-pyridazinyl 682 CH₂OCH₂CH═CH 4-pyridazinyl 683 CH₂OCH₂CH═CH 2-(2H-1,3-oxazinyl) 684 CH₂OCH₂CH═CH 2-(6H-1,3-oxazinyl) 685 CH₂OCH₂CH═CH 4-(6H-1,3-oxazinyl) 686 CH₂OCH₂CH═CH 6-(6H-1,3-oxazinyl) 687 CH₂OCH₂CH═CH [1,3,5]-2-triazinyl 688 CH₂OCH₂CH═CH [1,2,4]-3-triazinyl 689 CH₂OCH₂CH═CH [1,2,4]-5-triazinyl 690 CH₂OCH₂CH═CH [1,2,4]-6-triazinyl 691 CH═CHCH₂O oxiranyl 692 CH═CHCH₂O 3-methyl-2-oxiranyl 693 CH═CHCH₂O 2-oxetanyl 694 CH═CHCH₂O 3-hydroxy-3-methyl-2-oxetanyl 695 CH═CHCH₂O 3-hydroxy-3-ethyl-2-oxetanyl 696 CH═CHCH₂O 3-hydroxy-3-propyl-2-oxetanyl 697 CH═CHCH₂O 3-hydroxy-3-butyl-2-oxetanyl 698 CH═CHCH₂O 3-methoxy-3-methyl-2-oxetanyl 699 CH═CHCH₂O 3-methoxy-3-ethyl-2-oxetanyl 700 CH═CHCH₂O 3-methoxy-3-propyl-2-oxetanyl 701 CH═CHCH₂O 3-methoxy-3-butyl-2-oxetanyl 702 CH═CHCH₂O 3-trimethyl- silyloxy-3-methyl-2-oxetanyl 703 CH═CHCH₂O 3-trimethyl- silyloxy-3-ethyl-2-oxetanyl 704 CH═CHCH₂O 3-trimethyl- silyloxy-3-propyl-2-oxetanyl 705 CH═CHCH₂O 3-trimethyl- silyloxy-3-butyl-2-oxetanyl 706 CH═CHCH₂O 3-oxetanyl 707 CH═CHCH₂O 2-furyl 708 CH═CHCH₂O 4,5-dihydro-2-furyl 709 CH═CHCH₂O 2,3-dihydro-2-furyl 710 CH═CHCH₂O 3-furyl 711 CH═CHCH₂O 4,5-dihydro-3-furyl 712 CH═CHCH₂O 2,3-dihydro-3-furyl 713 CH═CHCH₂O 2-thienyl 714 CH═CHCH₂O 4,5-dihydro-2-thienyl 715 CH═CHCH₂O 2,3-dihydro-2-thienyl 716 CH═CHCH₂O 5-chloro-2-thienyl 717 CH═CHCH₂O 5-methyl-2-thienyl 718 CH═CHCH₂O 3-thienyl 719 CH═CHCH₂O 4,5-dihydro-3-thienyl 720 CH═CHCH₂O 2,3-dihydro-3-thienyl 721 CH═CHCH₂O 2-pyrrolyl 722 CH═CHCH₂O 2,5-dihydro-2-pyrrolyl 723 CH═CHCH₂O 3-pyrrolyl 724 CH═CHCH₂O 2,5-dihydro-3-pyrrolyl 725 CH═CHCH₂O 3-isoxazolyl 726 CH═CHCH₂O 4-methyl-3-isoxazolyl 727 CH═CHCH₂O 5-methyl-3-isoxazolyl 728 CH═CHCH₂O 4,5-dimethyl-3-isoxazolyl 729 CH═CHCH₂O 4,5-dihydro-3-isoxazolyl 730 CH═CHCH₂O 4-methyl-4,5-dihydro-3-isoxazolyl 731 CH═CHCH₂O 5-methyl-4,5-dihydro-3-isoxazolyl 732 CH═CHCH₂O 4,5-dimethyl-4,5-dihydro-3-isoxazo- lyl 733 CH═CHCH₂O 4-isoxazolyl 734 CH═CHCH₂O 3-methyl-4-isoxazolyl 735 CH═CHCH₂O 5-methyl-4-isoxazolyl 736 CH═CHCH₂O 5-cyclopropyl-4-isoxazolyl 737 CH═CHCH₂O 5-phenyl-4-isoxazolyl 738 CH═CHCH₂O 3,5-dimethyl-4-isoxazolyl 739 CH═CHCH₂O 4,5-dihydro-4-isoxazolyl 740 CH═CHCH₂O 3-methyl-4,5-dihydro-4-isoxazolyl 741 CH═CHCH₂O 5-methyl-4,5-dihydro-4-isoxazolyl 742 CH═CHCH₂O 3,5-dimethyl-4,5-dihydro-4-isoxazo- lyl 743 CH═CHCH₂O 5-isoxazolyl 744 CH═CHCH₂O 3-methyl-5-isoxazolyl 745 CH═CHCH₂O 4-methyl-5-isoxazolyl 746 CH═CHCH₂O 3,4-dimethyl-5-isoxazolyl 747 CH═CHCH₂O 4,5-dihydro-5-isoxazolyl 748 CH═CHCH₂O 3-methyl-4,5-dihydro-5-isoxazolyl 749 CH═CHCH₂O 4-methyl-4,5-dihydro-5-isoxazolyl 750 CH═CHCH₂O 3,4-dimethyl-4,5-dihydro-5-isoxazo- lyl 751 CH═CHCH₂O 3-isothiazolyl 752 CH═CHCH₂O 4-methyl-3-isothiazolyl 753 CH═CHCH₂O 5-methyl-3-isothiazolyl 754 CH═CHCH₂O 4-isothiazolyl 755 CH═CHCH₂O 3-methyl-4-isothiazolyl 756 CH═CHCH₂O 5-methyl-4-isothiazolyl 757 CH═CHCH₂O 5-isothiazolyl 758 CH═CHCH₂O 3-methyl-5-isothiazolyl 759 CH═CHCH₂O 4-methyl-5-isothiazolyl 760 CH═CHCH₂O 2-oxazolyl 761 CH═CHCH₂O 4-oxazolyl 762 CH═CHCH₂O 5-oxazolyl 763 CH═CHCH₂O 2-thiazolyl 764 CH═CHCH₂O 4-thiazolyl 765 CH═CHCH₂O 5-thiazolyl 766 CH═CHCH₂O 3-pyrazolyl 767 CH═CHCH₂O 4-pyrazolyl 768 CH═CHCH₂O 1-methyl-3-pyrazolyl 769 CH═CHCH₂O 1-methyl-4-pyrazolyl 770 CH═CHCH₂O 1-methyl-5-pyrazolyl 771 CH═CHCH₂O 2-imidazolyl 772 CH═CHCH₂O 1-methyl-2-imidazolyl 773 CH═CHCH₂O 5-methyl-[1,3,4]-2-oxadiazolyl 774 CH═CHCH₂O 5-methyl-[1,2,4]-3-oxadiazolyl 775 CH═CHCH₂O 5-methyl-[1,3,4]-2-thiadiazolyl 776 CH═CHCH₂O 5-methyl-[1,2,4]-3-thiadiazolyl 777 CH═CHCH₂O [1,2,4]-3-triazolyl 778 CH═CHCH₂O [1,2,3]-4-triazolyl 779 CH═CHCH₂O 2-pyridyl 780 CH═CHCH₂O 6-chloro-2-pyridyl 781 CH═CHCH₂O 6-methoxy-2-pyridyl 782 CH═CHCH₂O 6-trifluoromethyl-2-pyridyl 783 CH═CHCH₂O 3-pyridyl 784 CH═CHCH₂O 2-chloro-3-pyridyl 785 CH═CHCH₂O 2-methoxy-3-pyridyl 786 CH═CHCH₂O 4-pyridyl 787 CH═CHCH₂O 2-chloro-4-pyridyl 788 CH═CHCH₂O 2-methoxy-4-pyridyl 789 CH═CHCH₂O 2-ethoxy-4-pyridyl 790 CH═CHCH₂O 2-methylthio-4-pyridyl 791 CH═CHCH₂O 2-trifluoromethyl-5-pyridyl 792 CH═CHCH₂O 2-pyrimidinyl 793 CH═CHCH₂O 3-pyrimidinyl 794 CH═CHCH₂O 4-pyrimidinyl 795 CH═CHCH₂O 2-pyrazinyl 796 CH═CHCH₂O 3-pyridazinyl 797 CH═CHCH₂O 4-pyridazinyl 798 CH═CHCH₂O 2-(2H-1,3-oxazinyl) 799 CH═CHCH₂O 2-(6H-1,3-oxazinyl) 800 CH═CHCH₂O 4-(6H-1,3-oxazinyl) 801 CH═CHCH₂O 6-(6H-1,3-oxazinyl) 802 CH═CHCH₂O [1,3,5]-2-triazinyl 803 CH═CHCH₂O [1,2,4]-3-triazinyl 804 CH═CHCH₂O [1,2,4]-5-triazinyl 805 CH═CHCH₂O [1,2,4]-6-triazinyl 806 —C≡C—CH₂O oxiranyl 807 —C≡C—CH₂O 3-methyl-2-oxiranyl 808 —C≡C—CH₂O 2-oxetanyl 809 —C≡C—CH₂O 3-hydroxy-3-methyl-2-oxetanyl 810 —C≡C—CH₂O 3-hydroxy-3-ethyl-2-oxetanyl 811 —C≡C—CH₂O 3-hydroxy-3-propyl-2-oxetanyl 812 —C≡C—CH₂O 3-hydroxy-3-butyl-2-oxetanyl 813 —C≡C—CH₂O 3-methoxy-3-methyl-2-oxetanyl 814 —C≡C—CH₂O 3-methoxy-3-ethyl-2-oxetanyl 815 —C≡C—CH₂O 3-methoxy-3-propyl-2-oxetanyl 816 —C≡C—CH₂O 3-methoxy-3-butyl-2-oxetanyl 817 —C≡C—CH₂O 3-trimethyl- silyloxy-3-methyl-2-oxetanyl 818 —C≡C—CH₂O 3-trimethyl- silyloxy-3-ethyl-2-oxetanyl 819 —C≡C—CH₂O 3-trimethyl- silyloxy-3-propyl-2-oxetanyl 820 —C≡C—CH₂O 3-trimethyl- silyloxy-3-butyl-2-oxetanyl 821 —C≡C—CH₂O 3-oxetanyl 822 —C≡C—CH₂O 2-furyl 823 —C≡C—CH₂O 4,5-dihydro-2-furyl 824 —C≡C—CH₂O 2,3-dihydro-2-furyl 825 —C≡C—CH₂O 3-furyl 826 —C≡C—CH₂O 4,5-dihydro-3-furyl 827 —C≡C—CH₂O 2,3-dihydro-3-furyl 828 —C≡C—CH₂O 2-thienyl 829 —C≡C—CH₂O 4,5-dihydro-2-thienyl 830 —C≡C—CH₂O 2,3-dihydro-2-thienyl 831 —C≡C—CH₂O 5-chloro-2-thienyl 832 —C≡C—CH₂O 5-methyl-2-thienyl 833 —C≡C—CH₂O 3-thienyl 834 —C≡C—CH₂O 4,5-dihydro-3-thienyl 835 —C≡C—CH₂O 2,3-dihydro-3-thienyl 836 —C≡C—CH₂O 2-pyrrolyl 837 —C≡C—CH₂O 2,5-dihydro-2-pyrrolyl 838 —C≡C—CH₂O 3-pyrrolyl 839 —C≡C—CH₂O 2,5-dihydro-3-pyrrolyl 840 —C≡C—CH₂O 3-isoxazolyl 841 —C≡C—CH₂O 4-methyl-3-isoxazolyl 842 —C≡C—CH₂O 5-methyl-3-isoxazolyl 843 —C≡C—CH₂O 4,5-dimethyl-3-isoxazolyl 844 —C≡C—CH₂O 4,5-dihydro-3-isoxazolyl 845 —C≡C—CH₂O 4-methyl-4,5-dihydro-3-isoxazolyl 846 —C≡C—CH₂O 5-methyl-4,5-dihydro-3-isoxazolyl 847 —C≡C—CH₂O 4,5-dimethyl-4,5-dihydro-3-isoxazo- lyl 848 —C≡C—CH₂O 4-isoxazolyl 849 —C≡C—CH₂O 3-methyl-4-isoxazolyl 850 —C≡C—CH₂O 5-methyl-4-isoxazolyl 851 —C≡C—CH₂O 5-cyclopropyl-4-isoxazolyl 852 —C≡C—CH₂O 5-phenyl-4-isoxazolyl 853 —C≡C—CH₂O 3,5-dimethyl-4-isoxazolyl 854 —C≡C—CH₂O 4,5-dihydro-4-isoxazolyl 855 —C≡C—CH₂O 3-methyl-4,5-dihydro-4-isoxazolyl 856 —C≡C—CH₂O 5-methyl-4,5-dihydro-4-isoxazolyl 857 —C≡C—CH₂O 3,5-dimethyl-4,5-dihydro-4-isoxazo- lyl 858 —C≡C—CH₂O 5-isoxazolyl 859 —C≡C—CH₂O 3-methyl-5-isoxazolyl 860 —C≡C—CH₂O 4-methyl-5-isoxazolyl 861 —C≡C—CH₂O 3,4-dimethyl-5-isoxazolyl 862 —C≡C—CH₂O 4,5-dihydro-5-isoxazolyl 863 —C≡C—CH₂O 3-methyl-4,5-dihydro-5-isoxazolyl 864 —C≡C—CH₂O 4-methyl-4,5-dihydro-5-isoxazolyl 865 —C≡C—CH₂O 3,4-dimethyl-4,5-dihydro-5-isoxazo- lyl 866 —C≡C—CH₂O 3-isothiazolyl 867 —C≡C—CH₂O 4-methyl-3-isothiazolyl 868 —C≡C—CH₂O 5-methyl-3-isothiazolyl 869 —C≡C—CH₂O 4-isothiazolyl 870 —C≡C—CH₂O 3-methyl-4-isothiazolyl 871 —C≡C—CH₂O 5-methyl-4-isothiazolyl 872 —C≡C—CH₂O 5-isothiazolyl 873 —C≡C—CH₂O 3-methyl-5-isothiazolyl 874 —C≡C—CH₂O 4-methyl-5-isothiazolyl 875 —C≡C—CH₂O 2-oxazolyl 876 —C≡C—CH₂O 4-oxazolyl 877 —C≡C—CH₂O 5-oxazolyl 878 —C≡C—CH₂O 2-thiazolyl 879 —C≡C—CH₂O 4-thiazolyl 880 —C≡C—CH₂O 5-thiazolyl 881 —C≡C—CH₂O 3-pyrazolyl 882 —C≡C—CH₂O 4-pyrazolyl 883 —C≡C—CH₂O 1-methyl-3-pyrazolyl 884 —C≡C—CH₂O 1-methyl-4-pyrazolyl 885 —C≡C—CH₂O 1-methyl-5-pyrazolyl 886 —C≡C—CH₂O 2-imidazolyl 887 —C≡C—CH₂O 1-methyl-2-imidazolyl 888 —C≡C—CH₂O 5-methyl-[1,3,4]-2-oxadiazolyl 889 —C≡C—CH₂O 5-methyl-[1,2,4]-3-oxadiazolyl 890 —C≡C—CH₂O 5-methyl-[1,3,4]-2-thiadiazolyl 891 —C≡C—CH₂O 5-methyl-[1,2,4]-3-thiadiazolyl 892 —C≡C—CH₂O [1,2,4]-3-triazolyl 893 —C≡C—CH₂O [1,2,3]-4-triazolyl 894 —C≡C—CH₂O 2-pyridyl 895 —C≡C—CH₂O 6-chloro-2-pyridyl 896 —C≡C—CH₂O 6-methoxy-2-pyridyl 897 —C≡C—CH₂O 6-trifluoromethyl-2-pyridyl 898 —C≡C—CH₂O 3-pyridyl 899 —C≡C—CH₂O 2-chloro-3-pyridyl 900 —C≡C—CH₂O 2-methoxy-3-pyridyl 901 —C≡C—CH₂O 4-pyridyl 902 —C≡C—CH₂O 2-chloro-4-pyridyl 903 —C≡C—CH₂O 2-methoxy-4-pyridyl 904 —C≡C—CH₂O 2-ethoxy-4-pyridyl 905 —C≡C—CH₂O 2-methylthio-4-pyridyl 906 —C≡C—CH₂O 2-trifluoromethyl-5-pyridyl 907 —C≡C—CH₂O 2-pyrimidinyl 908 —C≡C—CH₂O 3-pyrimidinyl 909 —C≡C—CH₂O 4-pyrimidinyl 910 —C≡C—CH₂O 2-pyrazinyl 911 —C≡C—CH₂O 3-pyridazinyl 912 —C≡C—CH₂O 4-pyridazinyl 913 —C≡C—CH₂O 2-(2H-1,3-oxazinyl) 914 —C≡C—CH₂O 2-(6H-1,3-oxazinyl) 915 —C≡C—CH₂O 4-(6H-1,3-oxazinyl) 916 —C≡C—CH₂O 6-(6H-1,3-oxazinyl) 917 —C≡C—CH₂O [1,3,5]-2-triazinyl 918 —C≡C—CH₂O [1,2,4]-3-triazinyl 919 —C≡C—CH₂O [1,2,4]-5-triazinyl 920 —C≡C—CH₂O [1,2,4]-6-triazinyl

The Tables 1-144 below are based on the 4-benzoylpyrazoles of the formula Ib.

Table 1: Compounds 1.1-1.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 2: Compounds 2.1-2.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 3: Compounds 3.1-3.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 4: Compounds 4.1-4.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 5: Compounds 5.1-5.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 6: Compounds 6.1-6.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 7: Compounds 7.1-7.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 8: Compounds 8.1-8.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 9: Compounds 9.1-9.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 10: Compounds 10.1-10.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 11: Compounds 11.1-11.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 12: Compounds 12.1-12.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 13: Compounds 13.1-13.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 14: Compounds 14.1-14.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 15: Compounds 15.1-15.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 16: Compounds 16.1-16.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 17: Compounds 17.1-17.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 18: Compounds 18.1-18.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 19: Compounds 19.1-19.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 20: Compounds 20.1-20.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 21: Compounds 21.1-21.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 22: Compounds 22.1-22.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 23: Compounds 23.1-23.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 24: Compounds 24.1-24.920

Compounds of the formula Ib where R¹ is chlorine and R² is chlorine, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 25: Compounds 25.1-25.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 26: Compounds 26.1-26.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 27: Compounds 27.1-27.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 28: Compounds 28.1-28.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 29: Compounds 29.1-29.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 30: Compounds 30.1-30.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 31: Compounds 31.1-31.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 32: Compounds 32.1-32.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 33: Compounds 33.1-33.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 34: Compounds 34.1-34.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 35: Compounds 35.1-35.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 36: Compounds 36.1-36.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 37: Compounds 37.1-37.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 38: Compounds 38.1-38.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 39: Compounds 39.1-39.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 40: Compounds 40.1-40.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 41: Compounds 41.1-41.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 42: Compounds 42.1-42.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 43: Compounds 43.1-43.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 44: Compounds 44.1-44.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 45: Compounds 45.1-45.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 46: Compounds 46.1-46.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 47: Compounds 47.1-47.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 48: Compounds 48.1-48.920

Compounds of the formula Ib where R¹ is chlorine and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 49: Compounds 49.1-49.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 50: Compounds 50.1-50.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 51: Compounds 51.1-51.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 52: Compounds 52.1-52.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 53: Compounds 53.1-53.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 54: Compounds 54.1-54.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 55: Compounds 55.1-55.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 56: Compounds 56.1-56.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 57: Compounds 57.1-57.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 58: Compounds 58.1-58.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 59: Compounds 59.1-59.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 60: Compounds 60.1-60.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 61: Compounds 61.1-61.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 62: Compounds 62.1-62.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 63: Compounds 63.1-63.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 64: Compounds 64.1-64.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 65: Compounds 65.1-65.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 66: Compounds 66.1-66.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 67: Compounds 67.1-67.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 68: Compounds 68.1-68.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 69: Compounds 69.1-69.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 70: Compounds 70.1-70.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 71: Compounds 71.1-71.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 72: Compounds 72.1-72.920

Compounds of the formula Ib where R¹ is chlorine and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 73: Compounds 73.1-73.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 74: Compounds 74.1-74.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 75: Compounds 75.1-75.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 76: Compounds 76.1-76.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 77: Compounds 77.1-77.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 78: Compounds 78.1-78.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 79: Compounds 79.1-79.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 80: Compounds 80.1-80.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 81: Compounds 81.1-81.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 82: Compounds 82.1-82.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 83: Compounds 83.1-83.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 84: Compounds 84.1-84.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 85: Compounds 85.1-85.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 86: Compounds 86.1-86.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 87: Compounds 87.1-87.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 88: Compounds 88.1-88.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 89: Compounds 89.1-89.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 90: Compounds 90.1-90.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 91: Compounds 91.1-91.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 92: Compounds 92.1-92.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 93: Compounds 93.1-93.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 94: Compounds 94.1-94.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 95: Compounds 95.1-95.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is ethyl and R⁵ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 96: Compounds 96.1-96.920

Compounds of the formula Ib where R¹ is methyl and R² is chlorine, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 97: Compounds 97.1-97.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 98: Compounds 98.1-98.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 99: Compounds 99.1-99.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 100: Compounds 100.1-100.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 101: Compounds 101.1-101.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 102: Compounds 102.1-102.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 103: Compounds 103.1-103.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 104: Compounds 104.1-104.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 105: Compounds 105.1-105.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 106: Compounds 106.1-106.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 107: Compounds 107.1-107.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 108: Compounds 108.1-108.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 109: Compounds 109.1-109.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 110: Compounds 110.1-110.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 111: Compounds 111.1-111.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 112: Compounds 112.1-112.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 113: Compounds 113.1-113.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 114: Compounds 114.1-114.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 115: Compounds 115.1-115.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 116: Compounds 116.1-116.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 117: Compounds 117.1-117.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 118: Compounds 118.1-118.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 119: Compounds 119.1-119.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 120: Compounds 120.1-120.920

Compounds of the formula Ib where R¹ is methyl and R² is methylsulfonyl, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 121: Compounds 121.1-121.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁵ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 122: Compounds 122.1-122.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 123: Compounds 123.1-123.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is hydrogen and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 124: Compounds 124.1-124.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 125: Compounds 125.1-125.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 126: Compounds 126.1-126.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 127: Compounds 127.1-127.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 128: Compounds 128.1-128.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 129: Compounds 129.1-129.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 130: Compounds 130.1-130.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 131: Compounds 131.1-131.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 132: Compounds 132.1-132.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 133: Compounds 133.1-133.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 134: Compounds 134.1-134.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 135: Compounds 135.1-135.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethylcarbonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 136: Compounds 136.1-136.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 137: Compounds 137.1-137.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 138: Compounds 138.1-138.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is methylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 139: Compounds 139.1-139.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 140: Compounds 140.1-140.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 141: Compounds 141.1-141.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is ethylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 142: Compounds 142.1-142.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is methyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 143: Compounds 143.1-143.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is ethyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

Table 144: Compounds 144.1-144.920

Compounds of the formula Ib where R¹ is methyl and R² is trifluoromethyl, R⁵ is n-propyl and R⁶ is 4-methylphenylsulfonyl and where for each individual compound the substituents X¹ and Het correspond to one line of Table A.

The compounds I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and harmful grasses in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method used, the compounds I, or the compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum(N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

The herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The compounds I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend on the intended aims; in any case, they should guarantee a very fine distribution of the active compounds according to the invention.

Essentially, suitable inert auxiliaries include: mineral oil fractions of medium to high boiling point, such as kerosene and animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, eg. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, substituted 4-benzoylpyrazoles, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, eg. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active compounds together with a solid carrier.

Granules, eg. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the active compounds I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The compounds I according to the invention can be formulated for example as follows:

I. 20 parts by weight of the compound I are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

II. 20 parts by weight of the compound I are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

III. 20 parts by weight of the active compound I are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

IV. 20 parts by weight of the active compound I are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active compound.

V. 3 parts by weight of the active compound I are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active compound.

VI. 20 parts by weight of the active compound I are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound I is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound I is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (nonionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.

To widen the activity spectrum and to achieve synergistic effects, the substituted 4-benzoylpyrazoles I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds I, alone or else concomitantly in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

The active compound application rates are from 0.001 to 3.0, preferably 0.01 to 1.0 kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

The syntheses of some starting materials and products are described below.

2-Chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)phenyl)-4-sulfonylmethyl-(N-methyl-2-hydroxypyrazole)methanone.

Step a: Methyl 2-chloro-3-bromomethyl-4-sulfonylmethylbenzoate

80 g (0.3 mol) of methyl 2-chloro-3-methyl-4-sulfonylmethylbenzoate in 11 of carbon tetrachloride are heated at 76° C. together with 54 g (0.31 mol) of N-bromosuccinimide and 1.5 g of azoisobutyronitrile for 6 h. The reaction mixture is filtered and freed from the solvent under reduced pressure. Yield: 104 g; m.p. 83-85° C.

Step b: Methyl 2-chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)-4-sulfonylmethylbenzoate

3.3 g of 3,5-dimethylpyrazole and 4.2 g of potassium carbonate in 30 ml of N,N-dimethylformamide are heated at 70° C. for 1 h, admixed with a solution of 10 g (29.3 mmol) of methyl 2-chloro-3-bromomethyl-4-sulfonylmethylbenzoate in 100 ml of N,N-dimethylformamide, and the mixture is heated at 40° C. for 4 h. The reaction mixture is freed from the solvent under reduced pressure, taken up in ethyl acetate and washed with 5% strength aqueous sodium hydroxide solution. The organic phase is dried with sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 10.2 g; m.p. 90-95° C.

Step c: 2-Chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)-4-sulfonylmethylbenzoic acid

9.9 g (26.6 mmol) of methyl 2-chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)-4-sulfonylmethylbenzoate in a mixture of 50 ml of tetrahydrofuran and 50 ml of dist. water are treated at room temperature with 1.3 g of lithium hydroxide for 12 h. The reaction mixture is introduced into 300 ml of dist. water, adjusted to pH 1 using 10% strength aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic phases are dried with sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 6.2 g; m.p. 201-207° C.

Step d: 2-Chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)phenyl)-4-sulfonylmethyl-(N-methyl-2-hydroxypyrazole)methanone

2.0 g (5.6 mmol) of 2-chloro-3-(N-3,5-dimethylpyrazolyloxymethyl)-4-sulfonylmethylbenzoic acid, 0.6 g (5.6 mmol) of N-methyl-5-hydroxypyrazole and 1.4 g of N,N-dicyclohexylcarbodiimide in 50 ml of tetrahydrofuran are heated at 40° C. for 6 h. The reaction mixture is filtered and taken up in ethyl acetate. The organic phase is washed with saturated, aqueous sodium bicarbonate solution, dried with sodium sulfate, filtered and freed from the solvent under reduced pressure.

The crude product, together with 1.2 g of potassium carbonate, in 20 ml of 1,4-dioxane, is heated at 100° C. for 6 h. The reaction mixture is introduced into 500 ml of dist. water and extracted with diethyl ether. The organic phase is adjusted to pH 3 using 10% strength aqueous hydrochloric acid and extracted with dichloromethane. The organic phase is washed with dist. water, dried with sodium sulfate, filtered and freed from the solvent under reduced pressure. Yield: 1.5 g, m.p. 74° C.

TABLE 145

m.p. ¹H NMR No. R⁵ R⁶ X¹ Het [° C.] [ppm] 145.1 CH₃ H CH₂O 1-pyrazolyl 160 145.2 CH₃ iso- CH₂O 1-pyrazolyl 1.4 (d, 6 H); propyl 3.4 (s, 3 H); 3.7 (s, 3 H); 5.3 (m, 1 H); 6.1 (s, 2 H); 6.2 (d, 1 H); 7.2 (s, 1 H); 7.3 (s, 1 H); 7.4 (d, 1 H); 7.6 (d, 1 H); 8.2 (d, 1 H) 145.3 CH₃ H CH₂O 3,5-di-  74 methyl-1- pyrazolyl 145.4 CH₃ iso- CH₂O 3,5-di- 149 propyl methyl-1- pyrazolyl 145.5 CH₃ SO₂CH₃ CH₂O 3,5-di- 157 methyl-1- pyrazolyl 145.6 CH₃ H CH₂O 4-chloro- 164 1-pyrazolyl 145.7 CH₃ iso- CH₂O 4-chloro- 1.4 (d, 6 H); propyl 1-pyrazolyl 3.4 (s, 3 H); 3.7 (s, 3 H); 5.3 (m, 1 H); 6.1 (s, 2 H); 7.2 (dd, 2 H); 7.5 (s, 1 H); 7.6 (s, 1 H); 8.2 (d, 1 H) 145.8 CH₃ SO₂CH₃ CH₂O 4-chloro- 3.4 (s, 3 H); 1-pyrazolyl 3.6 (s, 3 H); 3.9 (s, 3 H); 6.1 (s, 2 H); 7.2 (s, 1 H); 7.4 (s, 1 H); 7.5 (s, 1 H); 7.6 (d, 1 H); 8.2 (d, 1 H) 145.9 CH₃ H CH₂O 2-pyridyl  94 145.10 CH₃ iso- CH₂O 2-pyridyl  66 propyl 145.11 C₂H₅ H CH₂O 1-pyrazolyl  63 145.12 C₂H₅ H CH₂O 2-pyridyl  90

USE EXAMPLES

The herbicidal activity of the substituted 4-benzoylpyrazoles of the formula I was demonstrated by greenhouse experiments:

The culture containers used were plastic pots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had een suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

The evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial parts and 0 means no damage, or normal course of growth. 

We claim:
 1. A 4-benzoylpyrazole of the formula I

where: R¹ and R² are each hydrogen, mercapto, nitro, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, —OR³, —OCOR³, —OSO₂R³, —S(O)_(n)R³, —SO₂OR³, —SO₂N(R³)₂, —NR³SO₂R³ or —NR³COR³; R³ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl or phenyl-C₁-C₆-alkyl; where the abovementioned alkyl radicals may be partially or fully halogenated and/or may carry one to three of the following groups: hydroxyl, mercapto, amino, cyano, R³, —OR³, —SR³, —N(R³)₂, ═NOR³, —OCOR³, —SCOR³, —NR³COR³, —CO₂R³, —COSR³, —CON(R³)₂, C₁-C₄-alkyliminooxy, C₁-C₄-alkoxyamino, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxy-C₂-C₆-alkoxycarbonyl, C₁-C₄-alkylsulfonyl heterocyclyl, heterocyclyloxy, phenyl, benzyl, hetaryl, phenoxy, benzyloxy and hetaryloxy, where the eight last-mentioned radicals may in turn be substituted; n is 0, 1 or 2; Q is a pyrazole of the formula II

 which is attached in position 4 and where R⁴ is hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl; R⁵ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, phenyl or phenyl which may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy; R⁶ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkylsulfonyl, phenylcarbonyl, phenylcarbonylmethyl, phenoxycarbonyl or phenylsulfonyl, where the four last-mentioned substituents are unsubstituted, or the phenyl ring in question may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy; X¹ is a straight-chain or branched C₁-C₆-alkylene, a C₂-C₆-alkenylene or a C₂-C₆-alkynylene chain which is interrupted by a hetero atom selected from the group consisting of: oxygen and sulfur, where the abovementioned alkylene, alkenylene or alkynylene radicals may be partially halogenated and/or may carry one to three of the following groups: —OR⁷, —OCOR⁷, —OCONHR⁷ or —OSO₂R⁷; R⁷ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, phenyl-C₁-C₆-alkyl, where the abovementioned alkyl, alkenyl or alkynyl radicals may be partially or fully halogenated and/or may be substituted by one or more of the following radicals: hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy; Het is a three- to six-membered partially or fully saturated heterocyclic group or a three- to six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups: nitrogen, oxygen in combination with at least one nitrogen or sulfur in combination with at least one nitrogen; where the abovementioned heterocyclic or heteroaromatic group may be partially or fully halogenated and/or may be substituted by R⁸; R⁸ is hydrogen, hydroxyl, mercapto, amino, cyano, nitro, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, where the alkyl radicals may in each case be substituted by in each case one or more of the following radicals: cyano, formyl, C₁-C₄-alkylamino, C₁-C₄-dialkylamino, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkylcarbonyl, C₁-C₄-alkylcarbonyloxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy; and agriculturally useful salts thereof.
 2. A 4-benzoylpyrazole of the formula I as claimed in claim 1, where R¹ is nitro, halogen, cyano, thiocyanato, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, —OR³ or —S(O)_(n)R³; R² is hydrogen or one of the radicals mentioned above under R¹.
 3. A 4-benzoylpyrazole of the formula Ia as claimed in claim 1 or 2,

where the substituents R¹, R², Q, X¹ and Het are each as defined under claim
 1. 4. A 4-benzoylpyrazole of the formula Ia as claimed in claim 3, where X¹ is a C₁-C₃-alkylene, C₂-C₃-alkenylene or C₂-C₃-alkynylene chain which is interrupted by an oxygen.
 5. A 4-benzoylpyrazole of the formula Ia as claimed in claim 3, where Het is a five- or six-membered partially or fully saturated heterocyclic or a five- or six-membered heteroaromatic group having up to three hetero atoms selected from the following three groups: nitrogen, oxygen in combination with at least one nitrogen or sulfur in combination with at least one nitrogen.
 6. A process for preparing 4-benzoylpyrazoles of the formula I as claimed in claim 1, which comprises acylating a pyrazole of the formula IIa, where the substituents R⁴ and R⁵ are each as defined under claim 1,

with an activated carboxylic acid IIIa or with a carboxylic acid IIIb,

where the substituents R¹, R², X¹ and Het are each as defined in claim 1 and L¹ is a nucleophilically replaceable leaving group, and rearranging the acylation product, optionally in the presence of a catalyst, to give the compounds I and, when R⁶ in formula I is not H, reacting these with a compound of the formula IV L²−R⁶  IV (where R⁶≠H) where R⁶ is as defined under claim 1 except for hydrogen and L² is a nucleophilically replaceable leaving group, to prepare 4-benzoylpyrazoles of the formula I where R⁶≠H.
 7. An activated carboxylic acid of the formula IIIa and a carboxylic acid of the formula IIIb as defined in claim
 6. 8. A composition comprising a herbicidally effective amount of at least one 4-benzoylpyrazole of the formula I or an agriculturally useful salt of I as claimed in claim 1 and auxiliaries which are customarily used for formulating crop protection agents.
 9. A process for preparing herbicidally active compositions as claimed in claim 8, which comprises mixing a herbicidally effective amount of at least one 4-benzoylpyrazole of the formula I or an agriculturally useful salt of I as claimed in claim 1 and auxiliaries which are customarily used for formulating crop protection agents.
 10. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one 4-benzoylpyrazole of the formula I or an agriculturally useful salt of I as claimed in claim 1 to act on plants, their habitat and/or on seeds. 